Solid-phase synthesis of 5,6-dihydropyrimidine-2,4-diones

被引:57
作者
Kolodziej, SA [1 ]
Hamper, BC [1 ]
机构
[1] MONSANTO CO,CEREGEN DIV,ST LOUIS,MO 63167
关键词
D O I
10.1016/0040-4039(96)01103-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 1,3-disubstituted-5,6-dihydropyrimidine- 1 are prepared by solid phase organic chemistry using a cyclization-cleavage strategy from readily available amines and isocyanates. An acrylate ester of Wangs resin is treated with primary amines to afford N-substituted beta-aminoesters followed by treatment with isocyanates to afford beta-ureido ester 4. Cyclization-cleavage of the bound ureido ester under acidic conditions gave direct formation of 5,6-dihydropyrimidinedione 1. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5277 / 5280
页数:4
相关论文
共 21 条
[1]   DIVERSOMERS - AN APPROACH TO NONPEPTIDE, NONOLIGOMERIC CHEMICAL DIVERSITY [J].
DEWITT, SH ;
KIELY, JS ;
STANKOVIC, CJ ;
SCHROEDER, MC ;
CODY, DMR ;
PAVIA, MR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) :6909-6913
[2]   Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization cleavage step [J].
Dressman, BA ;
Spangle, LA ;
Kaldor, SW .
TETRAHEDRON LETTERS, 1996, 37 (07) :937-940
[3]  
FUCHIKAMI T, 1985, SYNTHESIS-STUTTGART, P766
[4]   SYNTHESIS OF 1-ARYLURACILS [J].
GABEL, NW ;
BINKLEY, SB .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (04) :643-645
[5]   SOLID-PHASE SYNTHESIS OF HIGHLY SUBSTITUTED PEPTOID 1(2H)-ISOQUINOLINONES [J].
GOFF, DA ;
ZUCKERMANN, RN .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5748-5749
[6]   Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines [J].
Gordeev, MF ;
Patel, DV ;
Gordon, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :924-928
[7]   Strategy and tactics in combinatorial organic synthesis. Applications to drug discovery [J].
Gordon, EM ;
Gallop, MA ;
Patel, DV .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :144-154
[8]  
Ishii T., 1988, [No title captured], Patent No. [JP 63290867, 63290867]
[9]  
JOHNSON HW, 1959, J ORG CHEM, V24, P1391
[10]   COLOR TEST FOR TERMINAL PROLYL RESIDUES IN THE SOLID-PHASE SYNTHESIS OF PEPTIDES [J].
KAISER, E ;
BOSSINGER, CD ;
COLESCOTT, RL ;
OLSEN, DB .
ANALYTICA CHIMICA ACTA, 1980, 118 (01) :149-151